Some things about life are much better and easier when your father's a rich and successful senator, you don't really need to work for one thing, you have all the time and money you could ever want to indulge in whatever fun you want, others are less good, like being an only child in a household where your parents were never around. I was nineteen when the events of this story happened. My father, Senator Mark Feldman, had just been re-elected and was very busy all the time, some times spending days away from home when he had important business to attend to in the city. My mother, Madeleine Feldman, was the president of her own company and had a fortune that was at least an equal to my father. She, too, was a very busy woman, spending more time off at work than she ever spent at home. I don't know how great their sex life together was, although I suspect fairly non-existent, in fact it was a surprise to me how they ever managed to conceive me in the first place, they spent so little time in the same place at the same time. I tended to think that the only reason that they were still together was because they were both too busy to get a divorce or find someone else. I, Dean Feldman, was the only product of the marriage. I don't know whether I was unplanned, it seems unlike them to leave something like that to chance, but I do know that throughout my childhood they acted pretty much as if I was an unwanted burden on their precious time. I was raised by a succession of strict nannies, who never stayed around long enough for me to form any kind of bond with them. That continued until I was about 12, after which point I pretty much raised myself. My mother at least tried to take an interest in my schoolwork and encourage me those rare times when she was home early in the evening, but my father couldn't really care less about me, all he seemed to care about was advancing his political career.
Anyway, all this meant that through my teenage years I was pretty much left to my own devices, alone in our vast mostly unoccupied house. Having been brought up with little social interaction, I was, by nature, a shy boy and didn't really make friends very easily so I spent most of this time alone. Naturally, this resulted in me exploring and experimenting with aspects of myself that might have remained submerged under other circumstances. As it was, I was to discover that my shy, retiring personality had its outgoing, exhibitionist opposite buried deep within me. Itwas this personality that came out as I began to explore other things, things like the smooth, sensual sensations of wearing women's lingerie. I started out with just my mother's underwear, but as I explored the delights of the internet, I became bolder and began to order plenty of things of my own, I did, after all, have the advantage of my parents' vast wealth and plenty of time and opportunity. These were now things that would suit my feminine persona, sexy, vivacious, outgoing, dominant, everything my masculine persona was not. This was the way that "Delilah" was born. Of course, once I'd perfected how to dress, walk, talk and act like Delilah, there was no way that I was keeping her locked away at home. My parents were never around, so it wouldn't be difficult to go out and even spend whole days or nights living as Delilah. There may be another time to recount all the fun I had in those early days, discovering more and more about myself while the world discovered more and more of Delilah. Some time maybe I'll tell you about it, but for the purposes of this story all you need to know is that I was such a hit as Delilah that I got a job. As Dean I'd never had a job, I'd been too self indulgent to really want one and I didn't need the money, but this was a very special job. Delilah had been hired as a performer at a sex club that catered for people who liked their women with a little something extra. Delilah was a major hit with the people who frequented the club and soon I was the main act. Every Friday I would perform my act before an ever growing crowd of guys and girls, and some like me who were somewhere in between, simulating or actually having sex with my hot assistants or pulling punters out of the watching club to join me. Sometimes I would even ask them to join me for a private session later on. That's where this story begins, I'm nineteen, bored, rich, lonely, annoyed with my absentee parents, and leading a double life, as shy introverted layabout senator's son Dean, and feisty, sexy, crossdressing sex club star Delilah.
It was Friday and I knew well where I had to be. My mother was at home that evening but my father wasn't. The senator was busy at the office and would probably stay over in the city as he often did. I'd told my parents that I liked to go out on a Friday night in the city and that I'd always spend the night at my friend Delilah's place, that way they were never suspicious of what I was doing all those Fridays when I wasn't around. In my bedroom, I opened up my closet and found the bag where I kept Delilah's performance outfit. I was dressed in my normal masculine attire of jeans and a casual shirt, I would change at the club. I waved to my mother as I shut the door behind me and shut the door on this part of my life. I jumped into my little red sports car and drove off into town, leaving behind the suburb that represented the respectable, affluent side of my life, and heading for the sleazy club that would allow my dirty side to flourish.
It was getting dark when I arrived. The club was in a gay district and there were lots of couples of men and guys dressed as girls milling around outside the graphic neon signs. Looking at the wall I could see a poster with Delilah's photo on it, I smiled to myself, the transformation was so great that I doubted anyone else on the street would recognise the picture and me as the same person. A little electric thrill ran through me, I was already getting turned on by these thoughts and I hadn't even got dressed yet. I went around the back and was about to slip in the back entrance next to where the dressing rooms were, but was stopped by a tough, heavy set bouncer.
"Sorry, you can't go in there," he said, barring my way with his arm, "That's for performers and staff only."
I gave a girlish giggle and purred in my feminine voice, "Larry, it's me," he looked blank for a second before recognition flashed across his face,
"Delilah, sorry I didn't recognise you like that."
I smiled to myself once more, pleased with how total the transformation was, how totally separate these two personas of mine were. Little was I to know that tonight was when my two worlds came colliding together.
I got a dressing room to myself now I was the star, and this was where I headed in order to prepare for the evening's fun. First things first, I ran a hot bath and soaked myself in it, getting my body totally clean, washing away all residue of my life as Dean. Feeling totally clean and refreshed, I took a leg razor from my bag and proceeded to shave my legs, which were never exactly hairy, just covered in downy blonde hairs, but I needed to make them totally smooth, and the rest of my body, leaving my cock and balls totally shaved as well. Finally, I got out of the bath and wrapped myself in a towel. As I waited to become dry, I laid out my clothes for the evening, all tight shiny PVC, the dominatrix look was essential to my performance and to Delilah's character.
Now totally dry, I applied some glue to my chest and attached a pair of C-cup silicone breasts to my slender frame, instantly they changed my appearance from boyish to curvaceously feminine, I was well on the way to becoming Delilah. Next, I covered my waist and breasts in a tight black leather corset that laced at the front and turned my figure even more feminine, narrowing my waist to 26 inches, and pushing my breasts up so that they almost spilled out. I coupled this with a tiny black PVC mini-skirt that barely covered my thighs let alone all of my longlegs. The feel of leather and PVC on my skin was already making my cock twitch a little but there wasn't time for that now so I tucked it between my legs. I never wore panties to perform my act, although other times as Delilah I loved their silky sensual feel on my cock. Next were the gloves, also black PVC to match my skirt, they came all the way up to my elbows, and my crowning glory, the boots, which made up for my skirt's failure to cover anything by being thigh high so in fact much of my legs were clad in PVC. The tiny, sharp heels were six inches high and added to my height which was already almost six foot to enable me to tower dominantly over almost any man.
My outfit was ready, which left just my hair and make-up. Dramatic and slutty was the key to getting Delilah's make-up right and I'd had a lot of practice at it by now, giving her blushing red cheeks and deep, dark scarlet lips. I looked into the mirror and licked them eagerly, they were the kind of lips that were perfect to see wrapped around a hard cock. False eyelashes drew attention to my green eyes, as did lots of dramatic eye-shadow. Not that it mattered at all as the final transformation of my face involved covering the area around my eyes in a black mask. Finally, I topped the whole look off with my favourite wig, I could sense tonight might be something special, it was platinum blonde, far blonder than my natural hair, and long and wild and wavy. I struck a couple of sexy poses in the mirror, turning myself on a little so my cock was now semi-hard. I'd like to fuck that, I thought, and it thrilled me to know how many other men, and women, would be thinking the same thing soon. Having checked myself, I was ready to go out and perform. I grabbed my leather whip, my last accessory, and headed out into the hallway where I met Trish and Cindy who performed with me. Unlike me, just a crossdresser, these two were both authentic shemales with real breasts that I envied greatly, but I was still the star of the show so it didn't bother me too much. Cindy was a busty, short brunette and Trish was black, even taller than me with unnaturally massive breasts and a cock to match. They were both dressed in corsets and mini-skirts like mine.
